February 9, 2016

9 Most Famous Cross Dressers

Has it gotten any easier to live life as another gender, either publicly or discreetly? That topic is of much debate as social mores ebb and flow from era to era, as well as geographically. Well, history has no shortage of examples, from the modern to the ancient. Take a look at the folks who, out of necessity or desire, chose to live their lives as the opposite gender, sometimes for the sake of comedy or spectacle, and sometimes because that’s who they felt they were.

9. RuPaul

This 50 year-old drag queen reached her apex of popularity in the early-mid 90s, hosting a talk show and as a ubiquitous presence on awards shows and charity functions. Before his big break, he was a staple of the NYC and Atlanta club scenes in the late 80’s, and he went by his birth name, RuPaul Andre Charles.

RuPaul may have not been saving lives or fighting in wars but he/she (RuPaul has allowed either pronoun to be used in reference to him/her) was instrumental in mainstreaming the transgender/transvestite lifestyle to the MTV generation.

8. Milton Berle

Having lived until the ripe old age of 94, Berle clearly saw a lot of changes in his lifetime from 1908-2002. He had the distinction of being one of the US’s first television stars on Texaco Star Theater in the 40’s. How did he make such a name for himself? By dressing in drag, of course!

His cross-dressing shtick came from earlier vaudeville sensibilities, which were by no means edgy, but by introducing the concept to television, it reached many middle-American households that otherwise wouldn’t know what fun it was to dress up in women’s clothes!

7. Dorothy Lawrence

In a conventionally more noble pursuit, Dorothy Lawrence was an English reporter who was tired of getting denied access to the English troops on the front lines of WWI. She would circumvent this by enlisting in the English Army to gain the access she desired. However, the anxiety living this lie proved too much and she turned herself in after 10 days of service. She was arrested as a spy, but not charged, however, she was forbidden from writing on her experience, however brief. Her notes and thoughts were finally made public years later, though that defeated the purpose of her pursuit.

6. Norah Vincent

Again, the things women will do for the sake of journalism! Norah Vincent is a progressive journalist who had contributed to Slate, the LA Times, and the Village Voice. Earlier this decade, Vincent released a book Self-Made Man which chronicled 18 month of living as a man. She wanted to see how the other half lived. Vincent is a lesbian, but fonud that many features that made her considered “butch” in the gay community made her seem effeminate as a man. She even managed to date as a man, though I’m not sure how far those encounters went.

Damage was done, though, as she became clinically depressed as the experiment ended.

5. Hua Mulan

Whether or not “Mulan” was a real or fictional character is the matter of some debate, but the story is compelling enough to include it anyway, so let’s take a look. Mulan fought in her father’s place for the Chinese army for 12 years, ultimately refusing any rewards for her efforts. Of course, she had to maintain the appearance of a man during the whole affair, as women couldn’t fight.

Unfortunately, most of the primary texts discussing Mulan’s feats have disappeared, forcing us to get most of our information from folklore. And Disney movies.

4. J. Edgar Hoover

This hard-nosed FBI chief was known for maintaining files on virtually every person that had a semblance of interest about them. Turns out that J. Edgar was a pretty interesting guy himself, known for cross-dressing under the name “Muriel” in the late 50’s according to some socialites. It has never been definitively proven that he was a cross dresser or even gay, though he did attack anyone who made the mistake of any insinuations. It’s also been intimated that organized crime blackmailed Hoover with this info so as to escape his zealous prosecution. Yikes.

3. Chevalier d’Eon

This man was a French diplomat, freemason, and spy, having spent the first half (49 years, actually) as a man, then the remaining 33 as a woman until his death in 1810. Long life for those days!

Late in his career, he petitioned Louis XVI to be treated as and deemed a woman, despite having lived as a man up until that point. However, the court demanded that if he was considered to be a woman, he dress like a woman. They were insistent to the point that they even provided him funds for a new wardrobe. Understanding bunch, that French government.

2. Billy Lee Tipton

Billy Lee was a bandleader and jazz musician in America, having lived from 1914 to 1989. Born Dorothy Tipton, he lived his entire adult life as a man until his death. In fact, it wasn’t discovered until after his death that he had been a woman living as a man. Tipton took company with women throughout his life, identifying himself as straight.

1. George Sand

Born Amantine Lucile Aurore Dupin, Sand kept company with men (including Frederic Chopin) throughout her whole life, but took to wearing men’s clothing and adopting the clearly masculine name George Sand. Sand’s claim to fame was not only as a baroness, but as a novelist and memoir writer.

She also took to smoking tobacco in public, which, in Victorian France, was considered just as manly as wearing men’s clothes. Charles Beaudelaire was a particularly harsh detractor of not only her social habits, but her work as well, claiming, “She is stupid, heavy and garrulous. Her ideas on morals have the same depth of judgment and delicacy of feeling as those of janitresses and kept women…. The fact that there are men who could become enamoured of this slut is indeed a proof of the abasement of the men of this generation.”